I always refer back to this graphic in Alberto Gobbi's "Handling of
Tautomerism and Stereochemistry in Compound Registration" paper:
https://pubs.acs.org/doi/10.1021/ci200330x
[image: image.png]
@Greg Landrum , I would interpret "para
stereochemistry" as #3 in the above image. And "dependent stereochemistry"
as #2 in the above plot since the stereochemistry depends on the
stereochemistry of other centers.
Alberto's paper defines the above as:
1. steroegenic atom/chiral: typical right/left; R/S
2. pseudo-chiral (referencing an IUPAC paper and the gold book); note, the
same thing can happen with cis/trans double bond stereo, not depicted above
3. symmetric stereogenic centers
4. stereogenic bond: typical cis/trans; E/Z
5. atropisomers
TLDR: english is so imprecise, show me the SMILES. :-)
-Brian
On Thu, May 27, 2021 at 5:32 AM Greg Landrum wrote:
>
> I first heard the term "para stereochemistry" from Salome Rieder (a PhD
> student at the ETH Zurich), who pointed me to this paper as a source for
> term:
> https://pubs.acs.org/doi/pdf/10.1021/ci00016a003
>
> I tend to call this "dependent stereochemistry" since I think it's clear,
> but that's definitely something I just made up. :-)
>
> -greg
>
>
> On Wed, May 26, 2021 at 10:54 PM Jean-Marc Nuzillard <
> jm.nuzill...@univ-reims.fr> wrote:
>
>> Dear Paolo,
>>
>> According to https://goldbook.iupac.org/terms/view/P04921
>> your interpretation is certainly the correct one.
>> I still have to find how this r/s assignment is determined.
>>
>> Many thanks again,
>>
>> Jean-Marc
>>
>>
>> Le 26/05/2021 à 22:40, Paolo Tosco a écrit :
>> > Dear Jean-Marc,
>> >
>> > I believe it indicates what the IUPAC Gold Book refers to as
>> pseudoasymmetry.
>> > Let’s see if others agree with my interpretation.
>> >
>> > Cheers,
>> > P.
>> >
>> >> On 26 May 2021, at 22:28, Jean-Marc Nuzillard <
>> jm.nuzill...@univ-reims.fr> wrote:
>> >>
>> >> I believed I sent a message with the same title a few minutes ago,
>> but apparently something went wrong.
>> >>
>> >> Reading the RDKit book about function FindMolChiralCenters(),
>> >> I saw that it provides a better handling of para-stereochemisry.
>> >> This concept is not familiar to me.
>> >> Google did not help and sent me back to the RDKit Book.
>> >> So, what is para-stereochemistry?
>> >>
>> >> Best regards,
>> >>
>> >> Jean-Marc
>> >>
>> >> --
>> >> Jean-Marc Nuzillard
>> >> Directeur de Recherches au CNRS
>> >>
>> >> Institut de Chimie Moléculaire de Reims
>> >> CNRS UMR 7312
>> >> Moulin de la Housse
>> >> CPCBAI, Bâtiment 18
>> >> BP 1039
>> >> 51687 REIMS Cedex 2
>> >> France
>> >>
>> >> Tel : 03 26 91 82 10
>> >> Fax : 03 26 91 31 66
>> >> http://www.univ-reims.fr/icmr
>> >> http://eos.univ-reims.fr/LSD/CSNteam.html
>> >>
>> >> http://www.univ-reims.fr/LSD/
>> >> http://www.univ-reims.fr/LSD/JmnSoft/
>> >>
>> >>
>> >>
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>> --
>> Jean-Marc Nuzillard
>> Directeur de Recherches au CNRS
>>
>> Institut de Chimie Moléculaire de Reims
>> CNRS UMR 7312
>> Moulin de la Housse
>> CPCBAI, Bâtiment 18
>> BP 1039
>> 51687 REIMS Cedex 2
>> France
>>
>> Tel : 03 26 91 82 10
>> Fax : 03 26 91 31 66
>> http://www.univ-reims.fr/icmr
>> http://eos.univ-reims.fr/LSD/CSNteam.html
>>
>> http://www.univ-reims.fr/LSD/
>> http://www.univ-reims.fr/LSD/JmnSoft/
>>
>>
>>
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